
Rutland Vacations from ¥443,448
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The Latest Rutland Vacation Packages
Price found within the past 48 hours. Click for updated prices.

The Emily Hotel
Downtown Chicago
Price was ¥524,160, price is now ¥443,448 per person
¥443,448
per person
Aug 4 - Aug 9
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Staff was friendly, very nice property in a good walkable location
Reviewed on May 1, 2026

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ¥545,226, price is now ¥452,497 per person
¥452,497
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on May 12, 2026

Level Chicago - River North
Downtown Chicago
Price was ¥557,233, price is now ¥464,974 per person
¥464,974
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (984 reviews)
We loved the view from the 30th floor! The place was near the L, bus stops and walking distance to restaurants.. The bed was comfortable but it would be nice to have a table and lamp on both sides. The room seemed to be geared towards singles rather than couples. The espresso machine was a nice touch but fairly unusable for us. We ended up buying instant coffee and used the electric kettle. Sad that we couldn’t use the hot tub during our trip because it was closed for maintenance. But all in all, we were quite pleased with the apartment! Hubby spent a lot of time on the balcony enjoying the views. Highly recommend!
Reviewed on May 16, 2026

ENVITAE Hotel 4 Bedroom Luxury Apartments
Near North Side
Price was ¥689,948, price is now ¥581,171 per person
¥581,171
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (16 reviews)
⭐⭐⭐⭐⭐
We had a fantastic stay in this 4-bedroom apartment hotel. Looks exactly like the pictures. The unit was spotlessly clean and perfectly appointed — it truly felt like a home away from home. The kitchen had every amenity you could possibly need, which made cooking and relaxing with family incredibly easy.
The bedding was beautiful and very comfortable, and having a washer and dryer in the unit was a huge bonus, especially for a longer stay.
The building itself felt very secure, including the parking area, which gave us great peace of mind. We also loved the amenities — the gym and lounge area were excellent and well maintained.
Overall, this was one of the best apartment-style stays we’ve had. Comfortable, convenient, and thoughtfully set up. We would absolutely stay here again.
Reviewed on Mar 5, 2026
Find the Best Rutland Vacation Packages
Rutland Hotel Deals

The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is ¥19,858 per night from May 24 to May 25
¥19,858
¥22,938 total
May 24 - May 25
includes taxes & fees
9.4/10 Exceptional! (3,747 reviews)
Clean rooms, very nice accommodations, we will definitely stay here again.
Reviewed on May 17, 2026

DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is ¥16,056 per night from May 24 to May 25
¥16,056
¥18,545 total
May 24 - May 25
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
It was expensive because of the graduation prices, but it was still the most affordable option while still offering a healthy environment for me and my pet. The bar had excellent service, and the mac and cheese at the restaurant was the best I had ever had.
Reviewed on May 17, 2026

Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is ¥12,712 per night from May 31 to Jun 1
¥12,712
¥14,683 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,013 reviews)
Everything was clean and well put together. Comfortable and quiet...just how I liked it.
Reviewed on May 17, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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